Sarah Cooper on Drawing and Writing Insightful Satire

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Sarah Cooper is a writer, comedian, speaker, and creator of the satirical blog The Cooper Review. She built her comedy career in between working for companies like Yahoo! and Google.

Her new satirical book, How to Be Successful Without Hurting Men’s Feelings, comes out in October 2018. Her first book, 100 Tricks to Appear Smart in Meetings, was a hilarious look at office culture.

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You wrote several humor pieces that went viral on Medium (e.g. “10 Tricks to Appear Smart In Meetings”) and these paved the way for your website, The Cooper Review. How did you initially land on the hybrid approach of drawing and writing?

I really had no idea what I was doing when I first started The Cooper Review. 10 Tricks to Appear Smart in Meetings was text-only the first time I posted it on Medium, and most of my earlier posts were text-only as well. But one site I’ve always loved and kept coming back to was The Oatmeal. Everything Mathew Inman does is well written but also very visual, and it really inspired me. So within a few months, I started experimenting with making more visual posts.

My husband got me a Wacom tablet for Christmas the year I left Google and I started trying to draw. Unfortunately, I hated everything I drew! So I ended up discovering this hack of finding cheesy stock photos and tracing them. I think the cheesiness of the drawings sort of matched the faux business advice I was writing so it worked.

I released the illustrated version of 10 Tricks about 6 months later and it went viral again. That’s when it got the attention of publishers and literary agents. It was a good lesson in not being afraid to re-publish good content – new people will always discover it.

This helped me establish a style for The Cooper Review that people started to recognize which was great. Of course, now I’m kind of bored with the style so I want to start drawing freehand again. But I think I’ll always want to create visual posts. They take more time but they’re just more appealing to me.

Has your style of drawing led you to focus on certain types of comedic forms? For example, in your new book, How to Be Successful Without Hurting Men’s Feelings, you use a lot of side-by-side comparison drawings that make jokes about, say, office politics or gender double-standards. With the visual form, it makes comparisons easier. How your form (drawing and writing together) has led you down certain comedic paths?

The side-by-side comparison illustrations are basically a 2-panel cartoon that can be thought of as a setup and a punchline. This worked really well in my NYC vs SF illustrations as well. I think the main reason I like this style is because I have a short attention span and always prefer anything where I can get the joke in a few seconds. This is true for comedians I like (Mitch Hedberg is the best example) as well as online comics I like – check out Loryn Brantz of Buzzfeed, I love her stuff.

A lot of the writing I do is also advice (albeit bad advice) and parodies of infographics. I really love any form of parody so if I can take a set of charts and make them look like real charts but really they’re identifying the reasons why you want to take a nap now, I love that. I like the idea of making fun of whatever subject I’m tackling while also making fun of the cheesy visual style you see on a lot of “serious” websites.

I’ve noticed too that many of my more successful posts are the ones that are both funny and insightful. People like laughing but they love laughing and learning something even more. So I think the visual style is good for exposing truths in a fun, quick way.

When you picked up on the style of these serious business sites, was there any particular revelation like, “Oh, check out this Business Insider cartoon on how to negotiate a raise. This is so cheesy. I need to parody this style.”? Or was it more a general desire to poke fun at these types of sites?

There was an infographic called “How to Get People to Like You” which I just found so funny (and also sort of sad) that people were thinking this infographic was the key to having a likable personality. This idea that all your problems can be fixed in 10 easily digestible steps has always fascinated me. And also, yeah, it’s usually not that easy!

When creating a piece, do you typically start by drawing or writing first? I’m interested in which element is prior in your creative process.

I always start by writing first. I plan out the entire piece as much as possible before I get to the visuals because once I’m in Photoshop it is a black hole of time. I could literally play with fonts for days. So if I don’t have a good idea of what I’m trying to create and what the structure is, it’ll be that much harder to finish it. I think I’m also more of a writer at heart, so it’s usually me starting with an idea and trying to figure out how to make it visual, than the other way around. 

Do you have any writing habits or beliefs that others might consider weird or unusual?

I take a lot of naps. Okay, maybe all writers do that?

I think sleep is fundamental to creativity! What’s something that you’ve changed your mind about recently regarding your creative process?

I realized I need to get better at brainstorming. I tend to just want to let ideas hit me at random times but if I need to write something on a specific topic I need to get better at associating.

Some writers prefer the constraints of a specific topic, some don’t. Between The Cooper Review and your books, you’ve focused on corporate and office-related humor. What’s this been like for you creatively? Does it make things easier, since you have at least a broad world to start with for each piece? Does it ever feel constricting?

If you tell me to write about something specific I will come up with 8 other things I’d rather write about, trust me it’s very frustrating. It makes it hard for me to accept writing assignments or work on sponsored posts. It’s weird because I’m a youngest child and a people pleaser so I usually love being told what to do. Maybe it’s just my little form of rebellion 🙂

I started writing about office humor because that was just the world I was in. Being in meetings all day, working on teams, going to office events – I had a lot of material. So it didn’t feel like a stretch and I had ideas all the time. Now that I’m not working at a big company anymore, it’s not as easy to write about it. Yet, office humor is what people have come to expect from my site. So I’m kind of in a pickle.

But over the next year, I’m going to expand the site beyond office humor so I can write about whatever I’m inspired to write about depending on what’s going on in my life. I love that part about writing – whether it’s a blog post or standup comedy or a video – my writing and my stories will change just as I grow and change. Writing is something you can do whether you’re 18 or 80. I want to keep doing it until I’m 80, too. Maybe even 82.

What question do you ask yourself as a writer that you still haven’t answered yet?

I’m still searching for my voice as a stand-up comic and who I am on stage. This will just take a lot of practice and it’s a fun process. It’s also a very depressing process but I’m a glutton for punishment.

What do contemporary writers do that annoys you?

I hate how “thought leaders” write in very short sentences with lots of paragraph breaks.

Oh, I totally do that in short writing: tons of mini-grafs. Do you have any rules that you abide by as a writer? i.e. A personal code you follow.

As soon as I have an idea write it down no matter where I am or what I’m doing, otherwise I will forget it. When I sit down to write I always start from all the ideas I’ve written down, rather than a blank page. It helps jump-start the process.

What do those first jot-down ideas look like? Are they just quick phrases, or single sentences or jokes?

I write down a lot of standup comedy ideas – like:

“one great thing about being mixed ethnically is that I can get away with saying anything…but then I’m also offended by everything. I could say something racist but then I’d have to immediately report myself.”

And sometimes the beginnings of an article idea like:

“Be your authentic self at work today: don’t show up, sleep at your desk, tell Brian to go fuck himself”

Most are just inklings, very unfinished thoughts that need a lot of work, but a great place to start when I sit down to write.

What’s a belief that you used to have that held you back? How did you let go of it?

Thinking if it had been done before then there’s no point to me doing it. I made a video called “How to Cry on Cue,” and I made it before I realized how many other videos are out there on this subject. I thought about not publishing it because of that very reason but I went ahead anyway and now it’s one of my most popular videos. I finally realized that every person is unique and even if it’s been done before, if it’s never been done by you before, then that means it’s never been done.

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Get Sarah Cooper’s new book How to Be Successful Without Hurting Men’s Feelings. Learn more about Sarah Cooper at her website, and follow her on Twitter.

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Written by

Alex Baia is a humor writer and contributor to McSweeney’s and Slackjaw. He lives in Austin, TX.